A Family of Water-Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid

10Citations
Citations of this article
20Readers
Mendeley users who have this article in their library.

This article is free to access.

Abstract

Three dipolar aprotic solvents were designed to possess high dipolarity and low toxicity: N,N,N′,N′-tetrabutylsuccindiamide (TBSA), N,N′-diethyl-N,N′-dibutylsuccindiamide (EBSA), and N,N′-dimethyl-N,N′-dibutylsuccindiamide (MBSA). They were synthesized catalytically by using a K60 silica catalyst in a solventless system. Their water immiscibility stands out as an unusual and useful property for dipolar aprotic solvents. They were tested in a model Heck reaction, metal–organic framework syntheses, and a selection of polymer solubility experiments in which their performances were found to be comparable to traditional solvents. Furthermore, MBSA was found to be suitable for the production of an industrially relevant membrane from polyethersulfone. An integrated approach involving in silico analysis based on available experimental information, prediction model outcomes and read across data, as well as a panel of in vitro reporter gene assays covering a broad range of toxicological endpoints was used to assess toxicity. These in silico and in vitro tests suggested no alarming indications of toxicity in the new solvents.

Cite

CITATION STYLE

APA

Byrne, F. P., Nussbaumer, C. M., Savin, E. J., Milescu, R. A., McElroy, C. R., Clark, J. H., … Farmer, T. J. (2020). A Family of Water-Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid. ChemSusChem, 13(12), 3212–3221. https://doi.org/10.1002/cssc.202000462

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free